


Undercover

by amandateaches



Category: Supernatural
Genre: Case Fic, F/M, Fake Marriage, Fluff, Reader-Insert, Undercover
Language: English
Status: Completed
Published: 2018-12-30
Updated: 2018-12-30
Packaged: 2019-09-30 16:01:12
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,650
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17227055
Author URL: https://archiveofourown.org/users/amandateaches/pseuds/amandateaches
Summary: Dean and you are dancing around your feelings for each other when Sam finds a case that might just draw the two of you together.





	Undercover

**Author's Note:**

> This one is for two challenges. The first is @kas-not-cas’s 2.5k dialogue challenge. My prompt was “I can’t marry her. She’d kill me within a week!”. And, the second is for @itswitchcraft-not-googlemaps‘s Golden Girls 1.5k challenge. That prompt was Dorothy: “I have a date” Blanche: “With a man?” Dorothy: “No, Blanche. With a Venus Fly Trap.”

You trudged into the motel room just behind Sam and Dean, all three of you looking visibly exhausted. You had just wrapped up a week-long hunt, and you and the boys were running on fumes.

Sam peeled off from the group and walked over to the chair by the window to sit down, stretching his feet out in front of him. Dean, on the other hand, moved straight to the bed and fell face down on his stomach, letting out a long and dramatic groan. “I’m so tired, I think I could sleep for a week.”

Sam chuckled wearily. “A week already? On the drive home, it was only a day.”

“What can I say? I think I’m growing more tired by the second.” Dean said. “Besides, I think I deserve a week after that fight.”

You sat down on the bed beside him and laughed. “Take it easy, grandpa. It wasn’t that bad.”

“Oh, yeah?” he muttered. “That’s easy for you to say, Y/N. You didn’t have to be that vamp’s bait.”

“Oh, you big baby,” you said teasingly. “You loved being the center of attention.”

“Yeah, whatever,” Dean grumbled, turning to face you with a smile. “And, just for that ‘big baby’ crack, you get to make the beer run.”

You laughed again and stood up, stretching your arms up over your head, willing the fatigue away. “As tempting an offer as that is, I’m going to have to pass. I have a date.”

Dean sat up straight at that announcement, his fatigue suddenly gone. “With a man?”

You glared at him. “No, Dean. With a Venus Fly Trap. Yes, with a man!”

Sam laughed at that, drawing a glare from Dean. He immediately closed his mouth and looked down, a small smile still on his face. You looked at the two of them questioningly until Dean turned back to you.

“Who’s your date with?” Dean asked, his voice sounding uncharacteristically unsteady. You raised your eyebrow, but answered him anyway.

“That cute cop we met at the crime scene. Officer Pearson.”

“That moron?” Dean scoffed. “He couldn’t find his way out of a paper bag, let alone solve a crime. He’s not worth your time!”

“What are you talking about?” you asked. “I thought you liked Bryce? You said he was a good guy when we worked with him.”

Dean crossed his arms and frowned. “Well, I don’t like him now. You shouldn’t go out with him, Y/N. You can do better.”

You looked down. You knew you could do better. But, the only man that you were truly interested in only saw you as a friend: Dean. He was the only man for you, but he was more interested in the waitresses and barflies he met on the road than you. He always had been. You had long ago given up hoping that Dean would ever pick you.

So, when Bryce asked you out, you’d said yes. He was a nice enough guy, and he’d treat you to a good time. You knew it could never go anywhere, because he couldn’t make you forget about Dean, but it’d help for the night. “I appreciate your concern, Dean, but I’ll be fine. I’m a big girl.”

You waved goodbye and left to go to your room to shower and change, leaving Dean dismayed and Sam concerned. “You ok, man?”

Dean blinked twice before looking over at Sam. “Yeah. Why wouldn’t I be?”

“Because Y/N is going out on a date. With someone other than you.”

“Hey, Y/N and I are just friends. She can go out with whoever she wants.”

Sam rolled his eyes. “Come on, Dean. It’s me. You don’t have to hide your feelings.”

Dean frowned. “I hate when you go all psych on me, Sammy.”

Sam stared at him intently, until Dean finally gave in. “Fine! Yeah, it’s bugging me. I want to rip that guy’s throat out. But, there’s nothing I can do about it.”

“You can tell her how you feel.” He held up his hand before Dean could object. “Trust me, Dean, if the choice was between you and Bryce, she’d pick you.”

“I can’t,” he snapped back, before softening his tone. “What if something went wrong, Sammy? What if someone used her to get to me? It’s not like that hasn’t happened before. I can’t put her in jeopardy like that.”

Sam gave him a look filled with sympathy. “You can’t stop living life because you’re afraid.”

“I am not afraid!” Dean growled.

“Mmm hmm….” Sam muttered, unconvinced. “I’m just saying that if anyone deserves to be happy, it’s you and Y/N. You could make each other happy. You shouldn’t pass that up.”

“Yeah, whatever you say Dr. Phil,” Dean said sarcastically. He jumped up and walked towards the bathroom. “I don’t want to talk about this anymore. I’m gonna go take a shower.”

“I thought you were tired.”

“Not anymore!” Dean yelled over his shoulder before he slammed the bathroom door shut.

Sam sighed and ran his fingers through his hair. “Geez. Those two really are clueless.” He shook his head resignedly before opening up his laptop and getting to work on finding their next case.

The next morning, you sauntered into Sam and Dean’s room bright and early with three cups of coffee in your hand. Your date with Bryce had been boring, which was disappointing because you’d been hoping for a fun escape from your feelings for Dean, but, you had gotten a good night’s sleep, leaving you energized and ready for the day. So, the night hadn’t been a total loss.

You put the coffee on the table by the window and moved to pull open the curtains. Bright sunlight filled the room, causing both Sam and Dean to sit up and shield their eyes.

“Good morning!” you announced happily, turning towards them with a smile. Sam muttered a quiet ‘good morning’ in response and got up slowly, moving towards the coffee like it was a magnet.

Dean, on the other hand, laid back down with a groan. “Turn off that light…”

You laughed. “That light would be the sun.”

“Then turn off the sun,” he muttered before rolling back over and covering his eyes with a pillow.

You narrowed her eyes and bit your lip in concentration. Then, you walked past Sam, a clear purpose in your mind, and kneeled down on Dean’s bed, bouncing gently. “Come on, sleepyhead! Rise and shine!”

“Ugh…” he groaned, more gruffly this time. You kept bouncing, going faster in an attempt to get Dean to give in and get up. He started to bat at you with one of his hands, pushing you away, but you dodged his blows and continued to bounce.

After a minute, Sam stepped closer to the two of you with his warm smile in full effect, the coffee already taking a noticeable effect on his energy level. “Y/N’s right, Dean. You’ve got to get up. We have to hit the road. I found us a case.”

Those four words had Dean moving immediately, years’ worth of hunter instincts kicking in. He sat up quickly, nearly knocking you over. He reached out and steadied you before you could fall and pulled you gently towards him, throwing an arm around your shoulders to anchor you. “What case?”

As Sam answered him, you ducked out from under Dean’s arm and scooted towards the other end of the bed. You tried to ignore the way your heart sped up the second he touched you. Or the butterflies in your stomach when he pulled you against him. You were over Dean. It was just a little crush that you had under control. Going on that boring date last night proved that. Right?

Yup, this is healthy, you thought to yourself. Obsessing over Dean. Again. Time to snap out of it, Y/N.

You took a deep breath and tuned back into what Sam and Dean were saying.

“I can’t marry her!” you heard Dean exclaim. You turned to him, suddenly interested.

“Marry who?!”

Sam turned to you with a questioning look in his eyes. He was probably wondering why you hadn’t been listening. “You, Y/N. He needs to marry you. Well, pretend marry at least.”

“ME?! Why?”

“Like I said, we need someone to go undercover at the fundraiser to provide a distraction so I can get into the computer system. I can’t do it, because I need to get to the computer, so it has to be you and Dean.”

“Wait a second…” you said, holding up your hands. “Rewind and pause. What kind of a case is this?”

Sam sighed, but repeated himself calmly and patiently. “Last night, I was tracking some demon activity in Chicago. I traced it all back to one house, which seems to be the source.”

You shook your head, still confused. “Whose house is it?”

Dean responded very quietly and seriously, still looking straight at Sam. “Senator Geoffrey Cardin.”

“Whoa…” you whispered. Senator Cardin was one of the most powerful politicians in Washington. If he was a demon, that could only mean bad things.

“Yeah,” Dean said, echoing your shock.

Senator Cardin was currently running for reelection, which was probably why there was a fundraiser. A VIP only fundraiser. Sam had to have pulled a lot of strings to tickets to that. Probably pledging some money from a “big name donor” who would never end up paying up.

Suddenly, you had a thought. “Wait, why do we need to go undercover at the fundraiser? Can’t we just sneak in and gank him the old-fashioned way?”

Dean grinned and pointed at you. “I like that idea better.”

You nodded, but Sam sighed. “I already told you. I need to get into the records on his computer. He could have information on other demons, or even Crowley, that we could use to beat them. This is bigger than just one demon.”

“Fine,” Dean growled. “I understand that. But, why do Y/N and I need to pretend to be married?”

“The only tickets I could snag were for a couple, not two singles.”

“But, I can’t marry her. She’d kill me within a week!”

“Hey!” You yelled. You tried to ignore the hurt that tore through you at the realization that Dean couldn’t stand the thought of being married, even pretend married, to you, but it still stung.

Dean turned to you and gave you a small smile. “Oh, come on, Y/N. You know what I mean. No one would ever buy us as a couple. They’d see right through it.”

“Well, you’re just going to have to make it work,” Sam said firmly. “Because it’s the only option we’ve got.”

You looked over at the man you were in love with. How could you possibly get through this without messing everything up?

The next night, you were standing in front of the bathroom mirror in a motel on the outskirts of Chicago, IL, where Senator Cardin was throwing his campaign fundraiser at his massive estate. You smoothed out the fabric of the long, black, figure-hugging evening gown you had picked up that morning. You didn’t usually dress this extravagantly, so you felt incredibly self-conscious. It was bad enough that you had to pretend to be married to Dean all night without somehow slipping up and admitting that you loved him, but now you had to do it in a fancy dress and heels.

You sighed deeply, trying to will yourself to step outside the bathroom to meet Sam and Dean. “Let’s get this over with.”

You stepped through the doorway, your eyes instinctively seeking out Dean. He was standing by the door, with his back to you, talking to Sam. You couldn’t even see all of him, but you could already tell that he looked amazing in his tuxedo. Not that you were surprised.

You waited patiently until Sam looked up and saw you. He did a double take before grinning and gesturing for Dean to turn around.

When Dean turned, he had a frown on his face, probably from whatever Sam had been saying, but it instantly vanished the second he saw you. His jaw dropped and his eyes widened as his gaze moved down your body, taking in your outfit.

He didn’t say anything for a few seconds, as if he was trying to decide something. Your self-consciousness flew back, and you assumed he was trying to figure out how to tell you how awful you looked. “Does it look alright?”

Dean grinned, like he was suddenly sure about something. “Sam, can you give us a minute?”

Sam smiled knowingly and nodded before stepping out into the hall. You really started to worry then.

“Dean, what is it? Do I look horrible? I knew it. This is never going to work.”

Dean drew in a breath and walked towards you slowly, not stopping until he was right in front of you. “Y/N, you look beautiful. So beautiful, in fact, that I’m wondering why the hell I waited so long.”

You scrunched up your face. “Waited for what?”

“For this,” he whispered just before his lips crashed into yours. You stumbled in surprise, but he steadied you, pulling you into him. The second your body touched his, you melted, your arms sliding up to wrap around his neck and your mouth opening to respond to his. He took control, the heat and passion radiating from him and into you, making your knees go weak. It was a good thing he was holding you up, because, if anything was going to make you pass it, it was going to be a kiss from Dean Winchester. And, boy, did that man know how to kiss.

When the kiss was over, he pulled away, leaving you bemused and dumb-struck. “What….Why did you….What?”

Dean laughed quietly. “What?”

“You know what! Why did you kiss me?”

“Isn’t it obvious?”

“Dean…” you said warningly.

Dean grinned broadly and tightened his hold on you. “I kissed you because I wanted to. Because I like you, Y/N.”

Now it was your turn to smile. “You do?”

“Yeah, I do. Of course I do. How could I not? You’re beautiful, smart, funny. Kickass.” He added with a smile, drawing a laugh from you. “And seeing you standing there looking so drop-dead gorgeous in that dress, I couldn’t stand the thought of not kissing you.”

You leaned in to kiss him again but then thought better of it and pulled back, tilting your head up to look into his eyes. “But, wait a minute. If you liked me, then what was that, ‘I can’t marry her’ stuff about?”

He looked down, chagrined. “I was worried that if I had to pretend to be married to you, even for just a night, I wouldn’t be able to hide how I felt about you and I’d mess up our friendship. So, I said that to try to get Sam to drop the plan.”

You grinned and started laughing. “I was thinking the same thing about you!”

Dean started laughing along with you, before leaning in and silencing you both with a kiss. “I guess we really are alike.”

“I guess we are,” you whispered. You pulled back and grabbed the lapel of his suit jacket. “Let’s go show everyone just how in sync we are, husband, and when we get back, I’ll show you all the fantasies I was trying to hide from you.”

“Yes, ma’am!” Then he leaned in to devilishly whisper in your ear, his breath tickling you. “And, you’d better rest up now, because I’m have a feeling we’re going to be up allllll night.”

The way he said it didn’t sound like an idea, but like a promise. A promise you were more than happy to let him keep.


End file.
